Reduced calorie fat compositions containing polyol polyesters and reduced calorie triglycerides

ABSTRACT

Reduced calorie fat compositions which contain combinations of substantially nonabsorbable, substantially nondigestible polyol polyesters and certain reduced calorie triglycerides that function as anti-anal leakage agents and provide textural/taste benefits are disclosed. These reduced calorie fat compositions are useful in a variety of food applications, including frying oils for salted snacks, chocolate-flavored candy bars and cooking/salad oils.

This is a continuation of application Ser. No. 329,629, filed on Mar.28, 1989, now abandoned.

TECHNICAL FIELD

The present application relates to reduced calorie fat compositionswhich contain combinations of nonabsorbable, nondigestible polyolpolyesters and reduced calorie triglycerides that function as anti-analleakage agents and provide textural/taste benefits, e.g. lesswaxiness/greasiness, improved mouthmelt. The present application furtherrelates to food products, such as frying oils for salted snacks, firmchocolate-flavored products and cooking/salad oils, containingcombinations of these polyesters and triglycerides.

Polyol fatty acid polyesters are known in the art for use as low caloriesubstitutes for normal triglyceride fats. For example, Mattson et al.U.S. Pat. No. 3,600,186, issued Aug. 17, 1971, discloses low caloriefood compositions in which at least a portion of the fat content of aconventional food is provided by a nonabsorbable, nondigestible sugarfatty acid ester or sugar alcohol fatty acid ester having at least 4fatty acid ester groups with each fatty acid having from 8 to 22 carbonatoms. Foods in which these polyol polyesters are particularly usefulinclude salad and cooking oils, mayonnaise, margarine, dairy products,and plastic shortenings for use in frying, cake making, breadmaking orthe like.

Unfortunately, regular ingestion of moderate to high levels of liquidforms of these polyol polyesters can produce an undesirable laxativeside effect, namely, leakage of the polyesters through the analsphincter. Jandacek U.S. Pat. No. 4,005,195 issued Jan. 25, 1977discloses a means for preventing these undesirable laxative effectsthrough the addition of anti-anal leakage agents. These anti-analleakage or agents include solid fatty acids (melting point 37° C. orhigher) and their digestible triglyceride and ester sources, as well asedible solid, nondigestible, nonabsorbable polyol fatty acid polyesters.Solid fatty acids, solid triglycerides and solid polyol polyesters havedrawbacks when used as anti-anal leakage agents in low calorie foodcompositions. For example, a fatty acid, triglyceride or polyesterproviding a high solids content at body temperature tastes waxy in themouth when ingested. Additionally, cooking and salad oils containingsolid fatty acids, solid triglycerides or solid polyol polyesters can becloudy or opaque at room temperature, i.e., at about 70° F. (21.1° C.),or below, instead of clear. Accordingly, it would be desirable toprovide anti-anal leakage agents for liquid polyol polyesters which donot impart a waxy mouthfeel and can be used in formulating clear cookingoils.

BACKGROUND ART

Jandacek, U.S. Pat. No. 4,005,195 issued Jan. 25, 1977, disclosescompositions containing liquid polyol fatty acid polyesters andanti-anal leakage agents. The anti-anal leakage agents include solidfatty acids (melting point 37° C. or higher) and their triglyceride andester sources, specifically, edible C₁₂ and higher saturated fattyacids; and edible, nonabsorbable, nondigestible solid polyol fatty acidpolyesters having at least 4 fatty acid ester groups, wherein the polyolis selected from sugars and sugar alcohols containing from 4 to 8hydroxyl groups and wherein each fatty acid group has from about 8 toabout 22 carbon atoms. Examples of solid anti-anal leakage agentsspecifically disclosed are stearic acid, hydrogenated palm oil, andsucrose octastearate.

Jandacek et al, U.S. Pat. No. 4,005.196 issued Jan. 25, 1977, disclosesthe combination of liquid polyol polyesters, anti-anal leakage agents,and fat soluble vitamins selected from vitamin A, vitamin D, vitamin Eand vitamin K.

DISCLOSURE OF THE INVENTION

The present invention relates to reduced calorie fat compositions, whichcomprise:

a. from about 10 to about 65% of an edible, substantially nonabsorbable,substantially nondigestible polyol fatty acid polyester having at least4 fatty acid ester groups, wherein the polyol is selected from sugarsand sugar alcohols containing from 4 to 8 hydroxy groups and whereineach fatty acid group has from 2 to 24 carbon atoms; and

b. from about 35 to about 90% reduced calorie triglycerides selectedfrom MMM, MLM, MML, LLM, LML and LLL triglycerides, and mixturesthereof; wherein M is a saturated fatty acid residue selected from C₆ toC₁₀ saturated fatty acids, and mixtures thereof; wherein L is asaturated fatty acid residue selected from C₁₈ to C₂₄ saturated fattyacids, and mixtures thereof; wherein the reduced calorie triglyceridescomprise: (1) at least about 85% combined MLM, MML, LLM and LMLtriglycerides; and (2) up to about 15% combined MMM and LLLtriglycerides, and wherein the fatty acid composition of the reducedcalorie triglycerides comprises: (1) from about 10 to about 70% C₆ toC₁₀ saturated fatty acids; and (2) from about 30 to about 90% C₁₈ to C₂₄saturated fatty acids.

The present invention further relates to food products which comprisethese reduced calorie fat compositions as the sole fat ingredient, or incombination with other fat ingredients such as triglyceride oils. Thesefood products include frying oils for salted snacks and other friedfoods, firm chocolate-flavored products such as chocolate-flavored candybars or chips, as well as cooking and salad oils that are clear at roomtemperature, i.e., about 70° F. (21.1° C.), and preferably at lowertemperatures, e.g., at about 50° F. (10° C.).

Surprisingly, the reduced calorie triglycerides function as anti-analleakage agents for the polyol polyesters. In addition, the combinationof the polyol polyesters with the reduced calorie triglycerides providessignificant advantages over the use of either component alone. Theadvantages provided by these combinations include: (1) increased caloricreduction; (2) textural/taste benefits (e.g., less waxiness/greasiness,improved mouthmelt); (3) less color degradation during frying; and (4)less high temperature volatility and foaming during frying.

A. Definitions

By "substantially nondigestible, substantially non-absorbable" as usedherein is meant a polyol polyester which is about 30% or less digestedand absorbed. Preferred polyesters are about 10% or less digested andabsorbed.

By "reduced calorie triglycerides" as used herein is meant triglyceridesthat provide an at least about 10%, and preferably an at least about30%, reduction in calories relative to corn oil. These reduced calorietriglycerides usually provide between about 20% and about 50% reductionin calories. The reduction in calories provided by the present reducedcalorie triglycerides is based on the net energy gain (in Kcal) of ratsthat have ingested a diet containing a fat consisting of the reducedcalorie triglycerides, relative to the net energy gain (in Kcal) of ratsthat have ingested an identical diet, but containing corn oil instead ofthe fat consisting of the reduced calorie triglycerides. The test dietsused are nutritionally adequate to support both maintenance and growthof the rats. Total food intake and fat/oil intake are also matchedbetween the two diet groups so that differences in net carcass energygain are due entirely to the utilizable energy content of the fat/oil."Net energy gain" is based on the total carcass energy (in Kcal) of therats fed the test diet for some period of time (usually 4 weeks),reduced by the mean starting carcass energy (in Kcal) determined from astudy of a different group of rats of the same sex, strain, and similarbody weight fed a test diet that does not contain the fat/oil. "Totalcarcass energy" is determined by the dry carcass energy per gram (Kcalper gram) multiplied by the dry weight of the carcass (in grams)."Carcass energy per gram" is based on the carcass energy (in Kcal) asdetermined by bomb calorimetry of a homogeneous sample of the total drycarcass. All of these energy values are the average of a representativesample of rats (i.e., 10 rats).

By "medium chain saturated fatty acids," as used herein, is meantC_(6:0) (caproic), CB:_(8:0) (caprylic), or C_(10:0) (capric) fattyacids, or mixtures thereof. The C₇ and C₉ saturated fatty acids are notcommonly found, but they are not excluded from the possible medium chainfatty acids. The present medium chain fatty acids do not include lauricacid (C_(12:0)), sometimes referred to in the art as a medium chainfatty acid.

By "long chain saturated fatty acids," as used herein, is meant,C_(18:0) (stearic), C_(19:0) (nonadecylic), C_(20:0) (arachidic),C_(21:0) (heneicosanoic), C_(22:0) (behenic), C_(23:0) (tricosanoic), orC_(24:0) (lignoceric), or mixtures thereof.

In the above listing of fatty acid moieties, the common name of thefatty acid is given following its C_(x:y) designation (wherein x is thenumber of carbon atoms, and y is the number of double bonds).

By "MML," as used herein, is meant a triglyceride containing a longchain saturated fatty acid residue in the #1 or #3 position (an endposition) with two medium chain saturated fatty acid residues in theremaining two positions. (The absorption of long chain saturated fattyacids is generally reduced in the end positions.) Similarly, "MLM"represents a triglyceride with a long chain saturated fatty acid residuein the #2 position (the middle position) and two medium chain fatty acidresidues in the #1 and #3 positions, "LLM" represents a triglyceridewith a medium chain fatty acid residue in the #1 or #3 position and twolong chain fatty acid residues in the remaining two positions, and "LML"represents a triglyceride with a medium chain fatty acid residue in the#2 position and two long chain fatty acid residues in the #1 and #3positions.

By "MMM", as used herein, is meant a triglyceride containing mediumchain saturated fatty acid residues at all three positions. Similarly,"LLL" represents a triglyceride containing long chain saturated fattyacid residues at all three positions.

By "stearic MCT", as used herein, is meant a mixture of reduced calorietriglycerides according to the present invention that have been preparedby combining predominantly stearic acid (C_(18:0)) and medium chainsaturated fatty acids in some manner, for example by randomrearrangement of tristearin and medium chain triglycerides. The stearicMCT will contain predominantly stearic acid as the long chain saturatedfatty acid. By "behenic MCT" is meant a mixture of reduced calorietriglycerides that have been prepared by combining predominantly behenicacid (C_(22:0)) and medium chain saturated fatty acids, for example byrandom rearrangement of tribehenin and medium chain triglycerides. By"stearic/behenic MCT" is meant a mixture of reduced calorietriglycerides that have been prepared by combining predominantly stearicacid, behenic acid, and medium chain saturated fatty acids.

All percentages and proportions used herein are by weight unlessotherwise specified.

B. Polyol Fatty Acid Polyesters

The polyol fatty acid polyesters useful in the present inventioncomprise sugar fatty acid polyesters, sugar alcohol fatty acidpolyesters, and mixtures thereof, the sugars and sugar alcoholscontaining from 4 to 8 hydroxy groups prior to esterification. Sugar orsugar alcohol fatty acid polyesters comprise sugars or sugar alcohols,and fatty acids. The term "sugar" is used herein in its conventionalsense as generic to mono- and disaccharides. The term "sugar alcohol" isalso used in its conventional sense as generic to the reduction productof sugars wherein the aldehyde or ketone group has been reduced to analcohol. The polyol fatty acid polyesters are prepared by reacting amonosaccharide, disaccharide or sugar alcohol with fatty acids asdiscussed below.

Examples of suitable monosaccharides are those containing 4 hydroxygroups such as xylose, arabinose, and ribose; the sugar alcohol derivedfrom xylose, i.e., xylitol, is also suitable. The monosaccharideerythrose is not suitable for the practice of this invention since itonly contains 3 hydroxy groups; however, the sugar alcohol derived fromerythrose, i.e., erythritol, contains 4 hydroxy groups and is thussuitable. Among 5 hydroxy-containing monosaccharides that are suitablefor use herein are glucose, mannose, galactose, fructose, and sorbose. Asugar alcohol derived from sucrose, glucose, or sorbose, e.g., sorbitol,contains 6 hydroxy groups and is also suitable as the alcohol moiety ofthe polyester compounds. Examples of suitable disaccharides are maltose,lactose, and sucrose, all of which contain 8 hydroxy groups. Preferredpolyols for preparing the polyesters for use in the present inventionare selected from erythritol, xylitol, sorbitol, glucose and sucrose.Sucrose is especially preferred.

The polyol starting material having at least 4 hydroxy groups must haveat least 4 of these groups esterified with a fatty acid containing from2 to 24 carbon atoms, preferably from 8 to 22 carbon atoms, and mostpreferably from 12 to 18 carbon atoms. Examples of such fatty acidsinclude acetic, butyric, caproic, caprylic, capric, lauric, myristic,myristoleic, palmitic, palmitoleic, stearic, oleic, elaidic, ricinoleic,linoleic, linolenic, eleostearic, arachidonic, behenic, and erucic acid.The fatty acids can be derived from naturally occurring or syntheticfatty acids. They can be saturated or unsaturated, including positionalor geometrical isomers, e.g. cis- or trans-isomers. Suitable sources ofnaturally occurring fatty acids include soybean oil fatty acids, canolaoil fatty acids (i.e. fatty acids derived from low euricic acid rapeseedoil), sunflower seed oil fatty acids, sesame seed oil fatty acids,safflower oil fatty acids, palm kernel oil fatty acids, and coconut oilfatty acids.

The polyol fatty acid polyesters useful in the present invention mustcontain at least 4 fatty acid ester groups. Polyol fatty acid polyestercompounds that contain 3 or less fatty acid ester groups are digested inand the products of digestion are absorbed from the intestinal tractmuch in the manner of ordinary triglyceride fats, whereas the polyolfatty acid polyester compounds that contain 4 or more fatty acid estergroups are substantially nondigestible and consequently nonabsorbable bythe human body. It is not necessary that all of the hydroxy groups ofthe polyol be esterified with fatty acids, but it is preferable that thepolyol contain no more than 3 unesterified hydroxy groups, and morepreferable that it contain no more than 2 unesterified hydroxy groups.Most preferably, substantially all of the hydroxy groups of the polyolare esterified with fatty acid, i.e., the polyester is substantiallycompletely esterified. The fatty acids esterified to the polyol moleculecan be the same or mixed.

The present invention is particularly useful for polyol fatty acidpolyesters that are liquid (i.e., minimal or no Solid Fat Content) at atemperature of 98.6° F. (37° C.), i.e., body temperature, or below.Suitable liquid polyesters typically have a viscosity of about 2 poiseor less at 100° F. (37.8° C.) when measured at a shear rate of 10 sec⁻¹.These liquid polyesters typically contain fatty acid ester groups havinga high proportion of C₁₂ or lower fatty acid groups or else a highproportion of C₁₈ or higher unsaturated fatty acid groups. In the caseof those liquid polyesters having high proportions of unsaturated C₁₈ orhigher fatty acid groups, at least about half of the fatty acidsincorporated into the polyester molecule are typically unsaturated.Preferred unsaturated fatty acids in such liquid polyesters are oleicacid, linoleic acid, and mixtures thereof. The following are nonlimitingexamples of specific liquid polyol fatty acid polyesters suitable foruse in the present invention: sucrose tetraoleate, sucrose pentaoleate,sucrose hexaoleate, sucrose heptaoleate, sucrose octaoleate, sucroseoctaesters of soybean oil fatty acids (unsaturated), sucrose octaestersof canola oil fatty acids, sucrose octaesters of palm kernel oil orcoconut oil fatty acids, glucose tetraoleate, the glucose tetraesters ofor coconut oil soybean oil fatty acids (unsaturated), the mannosetetraesters of mixed soybean oil fatty acids, the galactose tetraestersof oleic acid, the arabinose tetraesters of linoleic acid, xylosetetralinoleate, galactose pentaoleate, sorbitol tetraoleate, thesorbitol hexaesters of unsaturated soybean oil fatty acids, xylitolpentaoleate, and mixtures thereof.

The polyol fatty acid polyesters need not be liquid at 98.6° F. (37° C.)to be useful in the present invention. For example, polyol polyestershaving the following properties are suitable: (a) a viscosity of fromabout 5 to about 800 poise, preferably from about 10 to about 100 poise,at 100° F. (37.8° C.) at a shear rate of 10 sec⁻¹ ; and (b) a Solid FatContent of from about 3 to about 20%, preferably from about 3 to about10%, at 98.6° F. (37° C.). As can be seen, these polyol esters are moreviscous and have an appreciable solids content at body temperaturescompared to liquid polyol polyesters. An example of such viscous polyolpolyesters is a sucrose octaester containing a mixture of soybeanhardstock and soybean oil fatty acids. See European patent application236,288 to Bernhardt, published Sept. 9, 1987 (herein incorporated byreference), particularly Examples 1 and 2 which disclose the preparationof sucrose octaesters from a mixture of fully hydrogenated (hardstock)and partially hydrogenated soybean oil fatty acid methyl esters.

Polyol fatty acid polyesters that are normally solid at bodytemperatures can also be useful in the present invention. Useful solidpolyol polyesters form a mixture with the reduced calorie triglycerides(as defined hereafter) that melts at or below 98.6° F. (37.8° C.) due toeutectic or solvent effects. An example of a solid polyester capable offorming such mixtures with the reduced calorie triglycerides is asucrose octaester having C₁₂ to C₁₄ fatty acid groups, and preferablypredominantly myristic acid groups (i.e. at least about 90% myristicacid, and most preferably at least about 95% myristic acid).

The polyol fatty acid polyesters suitable for use herein can be preparedby a variety of methods known to those skilled in the art. These methodsinclude: transesterification of the polyol with methyl, ethyl orglycerol fatty acid esters using a variety of catalysts; acylation ofthe polyol with a fatty acid chloride; acylation of the polyol with afatty acid anhydride; and acylation of the polyol with a fatty acid, perse. See, for example, U.S. Pat. No(s). 2,831,854, 3,600,186, 3,963,699,4,517,360 and 4,518,772, all of which are incorporated by reference,which disclose suitable methods for preparing polyol fatty acidpolyesters.

Specific, but nonlimiting, examples of the preparation of polyol fattyacid polyesters suitable for use in the practice of the presentinvention are as follows.

Erythritol tetraoleate: Erythritol and a five-fold molar excess ofmethyl oleate are heated at 180° C. under vacuum, with agitation, in thepresence of sodium methoxide catalyst over two reaction periods ofseveral hours each. The reaction product (predominately erythritoltetraoleate) is refined in petroleum ether and crystallized three timesfrom several volumes of acetone at 1° C.

Xylitol pentaoleate: Xylitol and a five-fold molar excess of methyloleate in dimethylacetamide (DMAC) solution are heated at 180° C. forfive hours in the presence of sodium methoxide catalyst, under vacuum.During this time the DMAC is removed by distillation. The product(predominately xylitol pentaoleate) is refined in petroleum ethersolution and, after being freed of petroleum ether, is separated as aliquid layer four times from acetone at about 1° C. and twice fromalcohol at about 10° C.

Sorbitol hexaoleate is prepared by essentially the same procedure usedto prepare xylitol pentaoleate except that sorbitol is substituted forxylitol.

Sucrose octaoleate is prepared by substantially the same procedure asthat used to prepare erythritol tetraoleate except that sucrose issubstituted for erythritol. Sucrose octaesters of soybean oil fattyacids: Soybean oil is partially hydrogenated to an iodine value of 107and then converted to the respective methyl esters. These methyl estersare then reacted with sucrose in the presence of a potassium carbonatecatalyst and the potassium soap of the soybean oil fatty acids.

Sucrose octaesters of canola oil fatty acids: Canola oil is partiallyhydrogenated to an iodine value of 90 and then converted to therespective methyl esters. These methyl esters are then reacted withsucrose at about 135° C. in the presence of a potassium carbonatecatalyst and the potassium soap of the canola oil fatty acids. SeeExample 1 of Volpenhein, U.S. Pat. No. 4,517,360, issued May 14, 1985.

Sucrose octaesters of soybean hardstock/soybean oil fatty acids: SeeExamples 1 and 2 of European patent application 236,288 to Bernhardt,published Sept. 9, 1987.

Sucrose octaesters of predominantly myristic acid: Myristic acid (atleast 99% pure) is converted to the respective methyl esters. Thesemethyl esters are then reacted with sucrose at about 135° C. in thepresence of a potassium carbonate catalyst and the potassium soap ofmyristic acid. See Example 2 (reaction conditions) and 1 (washconditions) of Volpenhein U.S. Pat. No. 4,517,360 issued May 14, 1985.

Sucrose octaesters of palm kernel oil fatty acids: Palm kernel oil(hydrogenated to an iodine value of about 4) is converted to therespective methyl esters. These methyl esters are then reacted withsucrose at about 135° C. in the presence of a potassium carbonatecatalyst and the potassium soap of the palm kernel oil fatty acids. SeeExample 1 of Volpenhein, U.S. Pat. No. 4,517,360, issued May 14, 1985.

C. Reduced Calorie Triglycerides

The reduced calorie triglycerides useful in the present invention areselected from MMM, MLM, MML, LLM, LML, and LLL triglycerides andparticularly mixtures thereof, wherein M is a saturated fatty acidresidue selected from C₆ to C₁₀ saturated fatty acids, and mixturesthereof, and L is a saturated fatty acid residue selected from C₁₈ toC₂₄ saturated fatty acids, and mixtures thereof. See U.S. applicationentitled "Reduced Calorie Fats Made from Triglycerides Containing Mediumand Long Chain Fatty Acids" to Paul Seiden, Ser. No. 329,620 P&G Case3760R), filed Mar. 28, 1989 (herein incorporated by reference), whichdiscloses reduced calorie fats comprising reduced calorie triglyceridesuseful in the present invention, and especially Examples 1 and 2 formethods for making same. The reduced calorie triglycerides comprise: (1)at least about 85%, preferably at least about 90%, and most preferablyat least about 95% combined MLM, MML, LLM and LML triglycerides.

For most fat compositions of the present invention, mono-long chaintriglycerides (MLM and MML) are usually preferred over di-long chaintriglycerides (LLM and LML), as well as the tri-long chain (LLL) andtri-medium chain (MMM) triglycerides. These preferred reduced calorietriglycerides comprise: (1) at least about 80%, preferably at leastabout 90% and most preferably at least about 95% combined MLM and MMLtriglycerides; (2) no more than about 10%, preferably no more than about5%, and most preferably no more than about 2% combined LLM and LMLtriglycerides; (3) no more than about 8%, preferably no more than about4%, and most preferably no more than about 3% MMM triglycerides; and (4)no more than about 2%, preferably no more than about 1%, and mostpreferably no more than about 0.5% LLL triglycerides.

In the reduced calorie triglycerides of the present invention, themedium chain fatty acids generally control the melting point of therespective triglyceride mixture. In particular, it has been found thatthese medium chain saturated fatty acids, when esterified onto theglycerol molecule, lower the melting point of the resultingtriglyceride. In addition, these medium chain fatty acids are readilyhydrolyzed (especially if attached at the #1 or #3 positions) bypancreatic lipase and then absorbed to provide a rapid energy source.However, these medium chain fatty acids, when metabolized, provide lesstotal calories (per gram) than the longer chain fatty acids.

The fatty acid composition of reduced calorie triglycerides useful inthe present invention comprise from about 10 to about 70%, preferablyfrom about 30 to 60%, and most preferably from about 40 to about 50% C₆to C₁₀ saturated fatty acids. The C₈ and C₁₀ saturated fatty acids aremost preferred for use in the reduced calorie triglycerides of thepresent invention. Preferably, the reduced calorie triglycerides containnot more than about 0.5% C₆ saturated fatty acid.

The other important fatty acid component of the reduced calorietriglycerides of the present invention are the C₁₈ to C₂₄ long chainsaturated fatty acids. These long chain saturated fatty acids, whenhydrolyzed from the respective triglyceride, are generally much morepoorly absorbed compared to the medium chain saturated fatty acids andthe long chain unsaturated fatty acids, e.g. linoleic acid. This isespecially true as the fatty acid increases in chain length from C₁₈(stearic) to C₂₂ (behenic) or higher. These poorly absorbed long chainfatty acids are generally solid at a temperature of 98.6° F. (37° C.).

The reduced calorie triglycerides of the present invention comprise fromabout 30 to about 90%, preferably from about 40 to about 70%, and mostpreferably from about 40 to about 60% C₁₈ to C₂₄ saturated fatty acids.For behenic MCT's, the reduced calorie triglycerides comprise from about20 to about 70%, and preferably from about 25 to about 50% C₂₀ to C₂₄long chain saturated fatty acids. Preferred behenic MCT's have fattyacid compositions which comprise no more than about 12%, and mostpreferably no more than about 9% C₂₀ to C₂₄ saturated fatty acids otherthan C₂₂ (behenic) saturated fatty acid. For stearic/behenic MCT's, thereduced calorie triglycerides preferably comprise from about 10 to about30% C₁₈ (stearic) saturated fatty acid.

The reduced calorie triglycerides of the present invention can containminor amounts of other fatty acids besides medium and long chainsaturated fatty acids, without losing the benefits of the presentinvention. For example, small amounts of C_(12:0), C_(14:0), C_(16:0),C_(18:2) and C_(18:3) fatty acids can be present. Palmitic acid(D_(16:0)) is about 95% absorbed by the body, while the longer chainsaturated fatty acids are less absorbed. Therefore, it is preferred thatthe reduced calorie triglycerides comprise no more than about 10%C_(16:0) fatty acid.

The reduced calorie triglycerides also typically comprise no more thanabout 6% fatty acids selected from C_(18:1), C_(18:2) and C_(18:3)unsaturated fatty acids, and mixtures thereof, and most preferably nomore than about 0.5%. Preferred reduced calorie triglycerides alsocomprise no more than about 3% fatty acids selected from C_(12:0)(lauric) and C_(14:0) (myristic) fatty acids, and mixtures thereof.Lauric and myristic acids result in more fat deposition than mediumchain saturated fatty acids.

Preferred stearic MCT's useful in the present invention comprise atleast about 80% triglycerides having carbon number of from C₃₄ to C₃₈,from about 40 to about 50% C₈ to C₁₀ saturated fatty acids and fromabout 35 to about 50% stearic acid. Preferred benehic MCT's comprise atleast about 80% triglycerides having carbon numbers of from C₃₈ to C₄₂,from about 40 to about 50% C₈ to C₁₀ saturated fatty acids and fromabout 40 to about 60% behenic acid. Preferred stearic/behenic MCT'spreferably comprise at least about 80% triglycerides having carbonnumbers of from C₃₄ to C₄₂, from about 40 to about 50% C₈ to C₁₀saturated fatty acids and from about 40 to about 60% combined stearicand behenic acid.

The reduced calorie triglycerides of the present invention can beprepared by a wide variety of techniques such as:

(a) random rearrangement of long chain triglycerides (e.g. tristearin ortribehenin) and medium chain triglycerides;

(b) esterification of glycerol with a blend of the corresponding fattyacids;

(c) transesterification of a blend of medium and long chain fatty acidmethyl esters with glycerol; and

(d) transesterification of long chain fatty acid glycerol esters (e.g.,glyceryl behenate) with medium chain triglycerides.

Random rearrangement of triglycerides is well-known in the art, as isthe esterification of glycerol with fatty acids. For discussions onthese subjects, see Hamilton et al., Fats and Oils: Chemistry andTechnology, pp. 93-96, Applied Science Publishers Ltd., London (1980),and Swern, Bailey's Industrial Oil and Fat Products, 3d ed., pp. 941-943and 958-965 (1964), both disclosures incorporated by reference herein.Transesterification is also discussed generally in Bailey's at pp.958-963.

Fatty acids per se or naturally occurring fats and oils can serve assources of fatty acids for preparing the reduced calorie triglycerides.For example, hydrogenated soybean oil and hydrogenated high erucic acidrapeseed oil are good sources of stearic and behenic acid, respectively.Odd chain length long chain saturated fatty acids can be found incertain marine oils. Medium chain saturated fatty acids can be obtainedfrom coconut, palm kernel, or babassu oils. They can also be obtainedfrom commercial medium chain triglycerides, such as the Captex 300 brandsold by Capital City Products, of Columbus, Ohio.

Tribehenin, useful for making the present reduced calorie triglycerides,can be prepared from behenic acid or from fractionated methyl behenateby esterification of the acid, or by transesterification of methylbehenate with glycerol. More importantly, blends of behenic acid andmedium chain saturated fatty acids can be esterified with glycerol.Other long chain saturated fatty acids (C₁₈, C₂₀, etc.) can be includedas well. Similarly, methyl ester blends can also be interesterified withglycerol.

The reduced calorie triglycerides can be modified to satisfy specificproduct performance requirements by additional fractionation. Solventand non-solvent crystal fractionation or fractional distillation methods(e.g. molecular distillation as described below) can be applied tooptimize performance. Standard fractionation methods are discussed inApplewhite, Bailey's Industrial Oil and Fat Products, Vol. 3, 4th ed.(1985), pp. 1-39, John Wiley & Sons, New York, incorporated by referenceherein. Molecular distillation can separate MML/MLM from LLM/LML-typetriglycerides, and can shift the carbon number concentration, but itcannot fractionate triglycerides having the same carbon number.Non-solvent or solvent crystal fractionation can also fractionateMLM/MML-type triglycerides from the higher melting LLM/LMLtriglycerides. The behenic MCT's fractionate without a solvent at about70° F. (21° C.), while the stearic/behenic MCT's fractionate at about60° F. (16° C.). Crystallization and filtration are usually repeated twoor three times.

Fractional distillation of the present reduced calorie triglycerides isnot limited to molecular distillation, but can also include conventionaldistillation (continuous or batch). After synthesis of the crudetriglyceride mixture, it is common to use a conventional batchdistillation technique to remove most of the excess medium chaintriglycerides, and then continue with molecular distillation. The vacuumrequirements are not as strict, and the temperature used can be higherin conventional distillation versus molecular distillation. Theconventional distillation temperature is generally between 405° F. (207°C.) and 515° F. (268.3° C.). The absolute pressure is less than 8 mm Hg,more preferably less than 2 mm Hg. The distillation is aided by spargingwith steam, nitrogen or other inert gas (e.g., CO₂). The distillation iscarried out to remove part of the excess MCT, most of the excess MCT, orto distill also the mono-long chain (MLM and MML) components.

Crystal fractionation of the fats can be carried out with and withoutsolvents, with and without agitation. The crystal fractionation can berepeated several times. Crystal fractionation is particularly effectiveto remove high melters. Fractionation of behenic MCT without solventscan be used to remove carbon number 50 and 52 LLM and LML components,which in turn alters the melting profile.

D. Reduced Calorie Fat Compositions

The present invention particularly relates to reduced calorie fatcompositions which are based on combinations of the polyol polyestersdefined in Section B with the reduced calorie triglycerides defined inSection C.

In the reduced calorie fat compositions of the present invention, theparticular level of polyol polyester that is included will depend on anumber of factors, including the application for which the compositionis used, the particular properties that are desired, as well as thephysical properties of the polyol polyester. Reduced calorie fatcompositions of the present invention can comprise from about 10 toabout 65% of such polyol polyesters. Preferred compositions comprisefrom about 10 to about 50% of such polyol polyesters, and mostpreferably from about 20 to about 40% of such polyesters. In the case ofliquid polyol polyesters, the fat composition preferably comprises fromabout 10 to about 40% of such polyol polyesters.

The particular polyol polyester used in the reduced calorie fatcompositions of the present invention will frequently depend on theparticular application in which it is used. For example, for cooking andsalad oils, liquid polyol polyesters are typically used such as sucroseoctaesters of soybean oil or canola oil fatty acids. Frying oils forsalted snacks and other fried foods also typically comprise liquidpolyol polyesters, alone or in combination with more viscous polyolpolyesters such as sucrose octaesters of soybean hardstock/soybean oilfatty acids. In the case of ice creams and ice cream coatings, sucroseoctaesters of palm kernel oil or coconut oil fatty acids are preferreddue to the sharper melting profile of the polyol polyester. For firmchocolate applications such as chocolate candy bars and chocolate chips,sucrose octaesters having predominantly myristic acid groups arepreferred.

In terms of caloric reduction, the polyol polyesters used in the fatcompositions of the present invention essentially provide minimal or nocalories since they are substantially nondigestible, and thereforesubstantially nonabsorbable. Unfortunately, regular ingestion ofmoderate to high levels of liquid versions of these polyesters canproduce undesirable "laxative" side effects, namely, leakage of thesepolyesters through the anal sphincter. As disclosed in Jandacek, U.S.Pat. No. 4,005,195, one way to prevent this undesirable laxative sideeffect is to include in the liquid polyol polyesters anti-anal leakage(AAL) agents which are completely solid at body temperature, includingsolid versions of these polyesters. However, inclusion of these solidAAL agents in the liquid polyesters at sufficiently high levels canimpart a less than desirable textural feel in the mouth typicallyreferred to as "waxiness". These solid AAL agents can also cause theresulting fat product, such as a cooking and salad oil, to be opaque,rather than clear at room temperature or below.

It has been surprisingly found that the reduced calorie triglyceridesdefined in Section C, when used in an effective amount, can provide AALbenefits for the liquid polyol polyesters, without at the same timeimparting an undesirable waxy mouthfeel. While not wishing to be boundby theory, it is believed that the saturated long chain fatty acidspresent in these reduced calorie triglycerides, when hydrolyzed bypancreatic lipase, form solid AAL materials in situ in the gut. Thesesolid long chain saturated fatty acids (or their soaps) act to bind theliquid polyol polyesters so as to avoid leakage through the analsphincter. The AAL benefit of these reduced calorie triglycerides isparticularly enhanced by the inclusion of small amounts (e.g., fromabout 0.05 to about 0.2% of the composition) of certain soaps ofsaturated C₁₂ and higher fatty acids, in particular soaps of stearic andbehenic fatty acids. These soaps include sodium and potassiumwater-soluble soaps, as well as calcium and magnesium water-insolublesoaps. Preferred soaps for inclusion in the reduced calorie fatcompositions of the present invention are calcium behenate and magnesiumstearate.

It is also believed that these reduced calorie triglycerides provide AALbenefits for fat compositions containing polyol polyesters that are moreviscous or solid at body temperatures. For example, sucrose octaestersof soybean hardstock/soybean oil fatty acids are still somewhat viscousat 98.6° F. (37° C.) due to an appreciable level of solids that bind theliquid portion of the polyesters. This viscous system is usuallysufficient to provide anal leakage control for nonheated applicationssuch as margarines, frozen desserts and the like. However, in heatedapplications, such as cooking or particularly frying, these sucroseoctaesters of soybean hardstock/soybean oil fatty acids can remainliquid for a sufficient period of time to cause a potential anal leakageproblem. Similarly, solid polyol polyesters that melt at or below 98.6°F. (37° C.) due to solvent/eutectic effects of the reduced calorietriglycerides may also be subject to potential leakage problems. It isbelieved the saturated long chain fatty acids present in the reducedcalorie triglycerides would prevent potential anal leakage of these moreviscous or solid polyol polyesters by a mechanism similar to that forthe liquid polyol polyesters.

The particular level of reduced calorie triglycerides required for AALbenefits will depend on the composition of the reduced calorietriglycerides, in particular the level of long chain saturated fattyacids present in the triglycerides, as well as the physical propertiesof the polyol polyester. To provide anti-anal leakage benefits, thereduced calorie triglycerides are included in the fat composition in anamount of from about 35 to about 90%. Preferably, these reduced calorietriglycerides are included in the fat composition in an amount of fromabout 50 to about 90%, and most preferably in an amount of from about 60to about 80%. Higher levels of these reduced calorie triglycerides,i.e., from about 60 to about 90%, are especially desirable to provideAAL benefits for liquid polyol polyesters.

In vivo testing is preferably used to determine the ability of thereduced calorie triglycerides to provide the desired AAL benefits. Insuch testing, animals are given a diet containing the reduced calorietriglycerides. The excreted lipids are checked to determine the amountof stearic/behenic acid present. The amount of excreted stearic/behenicacid is then compared against the amount present in the reduced calorietriglycerides prior to ingestion. Generally, the higher the ratio ofexcreted to ingested stearic/behenic acid, the more likely the reducedcalorie triglycerides will function as AAL agents.

For liquid polyol polyesters, the liquid/stability of a test composition(i.e., the liquid polyol polyesters and the respective fatty acids ofthe reduced calorie triglycerides in the proportions present in thereduced calorie fat composition) can be used, to a limited degree, topredict whether the desired AAL benefit can be obtained. By"liquid/solid stability" as used herein is meant that the liquid portionof the test composition does not readily separate from the solid portionat body temperature, i.e., the test composition appears to be a solideven though up to about 95% of it can be liquid. Liquid/solid stabilityis measured by centrifuging a sample of the test composition at 60,000rpm for one hour at 100° F. (37.8° C.). Liquid/solid stability isdefined as: 100% minus percentage of the test composition that separatedas a liquid after centrifuging. The viscosity of the test composition ismeasured at a shear rate of 10 sec⁻¹ over a 10 minute period. Testcompositions having a liquid/solid stability of at least about 90% wouldsuggest the respective reduced calorie fat composition has the desiredAAL benefit.

The combination of the reduced calorie triglycerides with the polyolpolyesters can also provide additional benefits. With regard to moreviscous or solid polyol polyesters, these reduced calorie triglyceridescan provide significant textural/taste benefits. For example, the moreviscous polyol polyesters such as the sucrose octaesters of soybeanhardstock/soybean oil fatty acids, have an appreciable level of solids,even at body temperatures. The reduced calorie triglycerides act as asolvent to reduce the level of solids in these more viscous polyolpolyesters at body temperatures. This imparts a less waxy/greasy tastewhen the reduced calorie fat composition is consumed. Even moresurprising are the benefits obtained with solid polyol polyesters, suchas sucrose octaesters containing predominantly myristic acid groups. Dueto solvent/eutectic effects, the reduced calorie triglycerides caneffectively lower the melting point of these solid sucrose octaesters to98.6° F. (37° C.) or below. This provides improved mouthmelt propertiesthat are particularly desirable for firm chocolate-flavored products.

With regard to liquid polyol polyesters, these reduced calorietriglycerides provide benefits in terms of less color degradation duringcooking and especially frying. Because liquid polyol polyesters used inthese compositions can include fairly high levels of unsaturated fattyacid residues, there is the possibility of oxidation and polymerizationof these unsaturated residues during cooking or frying. Because thereduced calorie triglycerides contain typically minimal levels ofunsaturated fatty acid levels, this oxidation and polymerization problemis minimized by their inclusion in place of the liquid polyolpolyesters. On the other hand, due to the high level of medium chainsaturated fatty acids present, these reduced calorie triglycerides tendto have lower smoke, flash and firepoint temperatures compared tostandard digestible triglycerides (e.g., soybean oil), as well aspotential foaming and autoignition problems, when used in cooking orfrying applications. On the other hand, the liquid polyol polyestershave much higher smoke, flash and firepoint temperatures. Accordingly,combinations of these liquid polyol polyesters with the reduced calorietriglycerides provide reduced calorie fat compositions which haveanti-anal leakage characteristics, improved color characteristics duringcooking or frying, while at the same time avoiding potential foaming andautoignition problems.

E. Uses of Reduced Calorie Fat Compositions

The reduced calorie fat compositions of the present invention can beused as a partial or total replacement for normal triglyceride fat inany fat-containing food product comprising fat and nonfat ingredients toprovide reduced calorie benefits. In order to obtain a significantreduction in calories, at least about 10%, and preferably at least about50%, of the total fat in the food product comprises the reduced caloriefat composition. On the other hand, very low calorie and thus highlydesirable food products of the present invention are obtained when thetotal fat comprises up to 100% of the reduced calorie fat composition.

The present reduced calorie fat compositions are useful in a widevariety of food and beverage products. For example, the fat compositionscan be used in the production of baked goods in any form, such as mixes,shelf-stable baked goods, and frozen baked goods. Possible applicationsinclude, but are not limited to, cakes, brownies, muffins, bar cookies,wafers, biscuits, pastries, pies, pie crusts, and cookies, includingsandwich cookies and chocolate chip cookies, particularly thestorage-stable dual-textured cookies described in Hong & Brabbs U.S.Pat. No. 4,455,333. The baked goods can contain fruit, cream, or otherfillings. Other baked goods uses include breads and rolls, crackers,pretzels, pancakes, waffles, ice cream cones and cups, yeast-raisedbaked goods, pizzas and pizza crusts, baked farinaceous snack foods, andother baked salted snacks.

In addition to their uses in baked goods, the reduced calorie fatcompositions can be used alone or in combination with other regular,reduced calorie or zero calorie fats to make shortening and oilproducts. The other fats can be synthetic or derived from animal orvegetable sources, or combinations of these. Shortening and oil productsinclude, but are not limited to, shortenings, margarines, spreads,butter blends, lards, cooking and frying oils, salad oils, popcorn oils,salad dressings, mayonnaise, and other edible oil products.

The present reduced calorie fat compositions have been found to beespecially useful as partial or complete replacements for digestibletriglyceride oils in frying oils used in preparing salted snackproducts, such as potato chips. Frying oils substituted with up to about60% of a more viscous polyol polyester (e.g., sucrose octaesters ofsoybean hardstock/soybean oil fatty acids) that inherently hassufficient solids at body temperatures to provide anal leakage controlhave been found to impart a more waxy mouthfeel to fried potato chips.Frying oils substituted with up to about 50% of a liquid polyolpolyester (e.g., sucrose octaesters of soybean oil fatty acids) havebeen found to be equivalent in waxiness impression to 100% triglyceridefrying oils, but with the potential risk of causing anal leakage. Fryingoils based on the present reduced calorie fat compositions permit theinclusion (in whole or in part) of liquid polyol polyesters to minimizethe waxy mouthfeel impression imparted to fried snack products, while atthe same time preventing anal leakage.

These frying oils can comprise from about 50 to 100% reduced calorie fatcomposition and from 0 to about 50% digestible triglyceride oil.Preferably, these frying oils comprise from about 75 to 100% reducedcalorie fat composition, and from 0 to about 25% digestible triglycerideoil. In addition to potato chips, these frying oils can be used in thepreparation of other salted snacks such as corn chips, tortilla chips,curls, puffs, potato sticks, french fries, and shoestring potatoes, aswell as other fried foods such as doughnuts, fried pies (e.g.,turnovers), crullers, fried meats (e.g., pork rinds and beef jerky),fried poultry (e.g., turkey and chicken) and fried seafood (e.g., shrimpand fish).

By "digestible triglyceride oil" as used herein is meant a triglycerideoil which is typically at least about 90% digestible and which has SolidFat Content (SFC) values of:

(a) about 1% or less at 50° F. (10° C.); and

(b) 0% at about 70° F. (21.1° C.).

The SFC values can be determined by heating the triglyceride oil to 140°F. (60° C.) for at least 20 minutes, tempering the heated oil at 32° F.(0° C.) for at least 5 minutes, further tempering the triglyceride oilat 80° F. (26.7° C.) for at least 30 minutes and then measuring thesolids content of the tempered oil by pulsed nuclear magnetic resonance(PNMR). See Madison et al, J. Amer. Oil Chem. Soc., Vol. 55 (1978), pp.328-31, which describes the method for measuring SFC values of a fat byPNMR.

Suitable digestible triglyceride oils can be derived from animal,vegetable or marine sources, including naturally occurring oils such ascottonseed oil, soybean oil, sunflower oil, corn oil, peanut oil,safflower oil, rapeseed oil, canola oil, and the like. Triglyceride oilsmost preferably used are soybean oil, safflower oil, sunflower oil,canola oil, and blends thereof. Triglyceride oils high in solids contentsuch as palm oil or hydrogenated vegetable oils usually need to bewinterized to provide suitable triglyceride oils having theabove-defined SFC values.

Certain of the present reduced calorie fat compositions are particularlyuseful in the formulation of firm chocolate-flavored products such aschocolate-flavored candy bars and chocolate-flavored chips. Reducedcalorie fat compositions useful in such products comprise from about 40to about 60% of a sucrose octaester having C₁₂ to C₁₄ fatty acid groups(preferably predominantly myristic acid groups) and from about 40 toabout 60% reduced calorie triglycerides (preferably behenic MCT's).Preferably, such reduced calorie fat compositions comprise from about 45to about 55% of such sucrose octaesters and from about 45 to about 55%of the reduced calorie triglycerides. Sucrose octaesters having C₁₂ toC₁₄ fatty acid groups, especially those having predominantly myristicacid groups, melt at a temperature above 98.6° F. (37° C.).Surprisingly, it has been found that the formulation of these sucroseoctaesters with reduced calorie triglycerides causes the resultingreduced calorie fat composition to melt at a temperature of about 98.6°F. (37° C.) or below. This lowering of melting point is believed to bedue to either eutectic or solvent effects.

Certain of these reduced calorie fat compositions are useful inproviding a portion of the total fat in cooking and salad oils which areclear at room temperature, i.e., at about 70° F. (21.1° C.), or below,e.g. at about 50° F. (10° C.). These cooking and salad oils comprise:

a. from about 2 to about 15% of a liquid polyol fatty acid polyester asdefined in Section B;

b. from about 5 to about 25% reduced calorie triglycerides as defined inSection C wherein the reduced calorie triglycerides comprise: (1) atleast about 80% combined MLM and MML triglycerides; (2) no more thanabout 10% combined LLM and LML triglycerides; (3) no more than about 8%MMM triglycerides; and (4) no more than about 2% LLL triglycerides; andwherein the fatty composition of the reduced calorie triglyceridescomprises: (1) from about 30 to about 60% C₆ to C₁₀ saturated fattyacids; (2) from about 10 to about 50% C₂₀ to C₂₄ saturated fatty acids;and (3) up to about 40% C₁₈ saturated fatty acid; and

c. from about 60 to about 90% of a digestible triglyceride oil aspreviously defined in this Section with regard to frying oils.

Preferred cooking and salad oils comprise from about 4 to about 12%liquid polyesters; from about 8 to about 20% reduced calorietriglycerides; and from about 68 to about 88% digestible triglycerideoil. Reduced calorie triglycerides for use in these preferred cookingand salad oils comprise at least about 90% (most preferably at leastabout 95%) combined MLM and MML triglycerides, no more than about 6%(most preferably no more than about 2%) combined LLM and LMLtriglycerides, no more than about 3% (most preferably no more than about2%) MMM triglycerides, no more than about 1% (preferably no more thanabout 0.5%) LLL triglycerides, from about 40 to about 50% CB to C₁₀saturated fatty acids, from about 10 to about 30% stearic acid, fromabout 20 to about 40% behenic acid, and no more than about 8% combinedC₂₀ and C₂₄ saturated fatty acids.

Other uses for the reduced calorie fat compositions of the presentinvention include partial or complete replacement for triglyceride fatand/or oils present in peanut butter, frozen desserts such as ice creamand ice cream coatings, whipped toppings, frosting products, processedmeat products, including vegetable protein-based meat analog products,sauces, gravies, and dairy products such as milkshakes, milk products,coffee whiteners, and cheese products.

The present reduced calorie fat compositions can also be fortified withvitamins and minerals, particularly the fat-soluble vitamins. MattsonU.S. Pat. No. 4,034,083 (incorporated by reference herein) disclosespolyol fatty acid polyesters fortified with fat-soluble vitamins. Thefat-soluble vitamins include vitamin A, vitamin D, vitamin E, andvitamin K. Vitamin A is a fat-soluble alcohol of the formula C₂₀ H₂₉ OH.Natural vitamin A is usually found esterified with a fatty acid;metabolically active forms of vitamin A also include the correspondingaldehyde and acid. Vitamin D is a fat-soluble vitamin well known for usein the treatment and prevention of rickets and other skeletal disorders.Vitamin D comprises sterols, and there are at least 11 sterols withvitamin D-type activity. Vitamin E (tocopherol) is a third fat-solublevitamin which can be used in the present invention. Four differenttocopherols have been identified (alpha, beta, gamma and delta), all ofwhich are oily, yellow liquids, insoluble in water but soluble in fatsand oils. Vitamin K exists in at least three forms, all belonging to thegroup of chemical compounds known as quinones. The naturally occurringfat-soluble vitamins are KI (phylloquinone), K₂ (menaquinone), and K₃(menadione). The amount of the fat-soluble vitamins employed herein tofortify the present fat compositions can vary. If desired, the fatcompositions can be fortified with a recommended daily allowance (RDA),or increment or multiple of an RDA, of any of the fat-soluble vitaminsor combinations thereof. It is preferred that shortenings and oilscontaining up to 35% by weight of sucrose fatty acid polyesters besupplemented with 1.1 mg. vitamin E in the form of d-alpha-tocopherolacetate per gram of sucrose polyester. If used for deep frying, theshortenings and oils preferably contain 0.88 mg. vitamin E per gram ofsucrose polyester.

Vitamins that are insoluble in fat can similarly be included in thepresent reduced calorie fat compositions. Among these vitamins are thevitamin B complex vitamins, vitamin C, vitamin G, vitamin H, and vitaminP. The minerals include the wide variety of minerals known to be usefulin the diet, such as calcium, magnesium, and zinc. Any combination ofvitamins and minerals can be used in the present reduced calorie fatcompositions.

The present reduced calorie fat compositions are particularly useful incombination with particular classes of food and beverage ingredients.For example, an extra calorie reduction benefit is achieved when the fatcompositions are used with noncaloric or reduced calorie sweetenersalone or in combination with bulking agents. Noncaloric or reducedcalorie sweeteners include, but are not limited to, aspartame;saccharin; alitame, thaumatin; dihydrochalcones; cyclamates;steviosides; glycyrrhizins, synthetic alkoxy aromatics, such as Dulcinand P-4000; sucrolose; suosan; miraculin; monellin; sorbitol, xylitol;talin; cyclohexylsulfamates; substituted imidazolines; syntheticsulfamic acids such as acesulfame, acesulfam-K and n-substitutedsulfamic acids; oximes such as perilartine; rebaudioside-A; peptidessuch as aspartyl malonates and succanilic acids; dipeptides; amino acidbased sweeteners such as gem-diaminoalkanes, meta-aminobenzoic acid,L-aminodicarboxylic acid alkanes, and amides of certainalpha-aminodicarboxylic acids and gem-diamines; and3-hydroxy-4-alkyloxyphenyl aliphatic carboxylates or heterocyclicaromatic carboxylates.

The reduced calorie fat compositions can be used in combination withother noncaloric or reduced calorie fats, such as branched chain fattyacid triglycerides, triglycerol ethers, polycarboxylic acid esters,sucrose polyethers, neopentyl alcohol esters, silicone oils/siloxanes,and dicarboxylic acid esters. Other partial fat replacements useful incombination with the fat materials are medium chain triglycerides,highly esterified polyglycerol esters, acetin fats, plant sterol esters,polyoxyethylene esters, jojoba esters, mono/diglycerides of fatty acids,and mono/diglycerides of short-chain dibasic acids.

Bulking or bodying agents are useful in combination with the reducedcalorie fat compositions in many food compositions. The bulking agentscan be nondigestible carbohydrates, for example, polydextrose andcellulose or cellulose derivatives, such as carboxymethylcellulose,carboxyethylcellulose, hydroxypropylcellulose, methylcellulose andmicrocrystalline cellulose. Other suitable bulking agents include gums(hydrocolloids), starches, dextrins, fermented whey, tofu,maltodextrins, polyols, including sugar alcohols, e.g. sorbitol andmannitol, and carbohydrates, e.g. lactose.

Similarly, food and beverage compositions can be made that combine thepresent reduced calorie fat compositions with dietary fibers to achievethe combined benefits of each. By "dietary fiber" is meant complexcarbohydrates resistant to digestion by mammalian enzymes, such as thecarbohydrates found in plant cell walls and seaweed, and those producedby microbial fermentation. Examples of these complex carbohydrates arebrans, celluloses, hemicelluloses, pectins, gums and mucilages, seaweedextract, and biosynthetic gums. Sources of the cellulosic fiber includevegetables, fruits, seeds, cereals, and man-made fibers (for example, bybacterial synthesis). Commercial fibers such as purified plantcellulose, or cellulose flour, can also be used. Naturally occurringfibers include fiber from whole citrus peel, citrus albedo, sugar beets,citrus pulp and vesicle solids, apples, apricots, and watermelon rinds.

These dietary fibers may be in a crude or purified form. The dietaryfiber used may be of a single type (e.g. cellulose), a composite dietaryfiber (e.g. citrus albedo fiber containing cellulose and pectin), orsome combination of fibers (e.g. cellulose and a gum). The fibers can beprocessed by methods known to the art.

Of course, judgment should be exercised to make use of appropriatereduced calorie fat compositions and combinations of the fatcompositions with other food ingredients. For example, a combination ofsweetener and fat composition would not be used where the specificbenefits of the two are not desired. The fat compositions and fatcomposition/ingredient combinations are used where appropriate, and inthe proper amounts.

Many benefits are obtained from the use of the present reduced caloriefat compositions in food and beverage compositions, either when usedalone or in combination with the ingredients discussed above. A primarybenefit is the calorie reduction achieved when the fat compositions areused as a total or partial fat replacement. This calorie reduction canbe increased by using combinations of the present fat compositions withreduced calorie sweeteners, bulking agents, or other reduced calorie ornoncaloric fats. Another benefit which follows from this use is adecrease in the total amount of fats in the diet. Foods or beveragesmade with the reduced calorie fat compositions instead of triglyceridefats will also contain less cholesterol, and the ingestion of thesefoods can lead to reduced serum cholesterol and thus reduced risk ofheart disease.

A related benefit is that the use of the reduced calorie fatcompositions allows the production of foods and beverages that arestable in terms of shelf stability and penetration stability.Compositions made with the reduced calorie fats have acceptableorganoleptic properties, particularly taste and texture.

Dietary foods can be made with the reduced calorie fat compositions tomeet special dietary needs, for example, of persons who are obese,diabetic, or hypercholesterolemic. The fat compositions can be a majorpart of a low-fat, low-calorie, low-cholesterol diet, and they can beused alone or in combination with drug therapy or other therapy.Combinations of food or beverage products made with the reduced caloriefat compositions can be used as part of a total dietary managementregimen, based on one or more of these products, containing the fatcompositions alone or in combination with one or more of theabove-mentioned ingredients, to provide one or more of theabove-mentioned benefits.

This discussion of the reduced calorie fat composition uses,combinations, and benefits, is not intended to be limiting orall-inclusive. It is contemplated that other similar uses and benefitscan be found that will fall within the spirit and scope of thisinvention.

It is known that certain fatty esters will inhibit the absorption ofcholesterol. The present invention also encompasses methods for loweringserum cholesterol by inhibiting the absorption of cholesterol withoutcausing an anal leakage effect, comprising systemically (generally,orally) administering to animals susceptible to or afflicted withhypercholesterolemia successive therapeutically effective doses of thereduced calorie fat compositions of the foregoing type. Generally thedosage is about 0.1 gram to about 5 grams of the present fatcompositions.

F. Analytical Methods

1. Viscosity Measurements

A. Sample Preparation

The polyol polyester is melted at about 160° F. (71.1° C.). A 3 gramsample of melted polyol polyester is weighed into a glass vial. The vialand its contents are heated to 160° F. (71.1° C.) and then immediatelytransferred to a controlled temperature room held at 100° F. (37.8° C.).The sample is then allowed to recrystallize at 100° F. (37.8° C.) for 24hours. After the 24 hour time period has elapsed, the sample is taken tothe viscometer in an insulated cup and the viscosity is measured.

Ferranti-Shirley Viscometer Operation Procedure

A Ferranti-Shirley viscometer is used for the viscosity measurement. Acone is put into place, and the viscometer temperature is adjusted to100° F. (37.8° C.). The chart recorder is calibrated, and the gapbetween the cone and plate is set. The cone speed is checked, and thecone and plate temperatures are equilibrated to 100° F. (37.8° C.). Thepanel controls are set. Sufficient sample is placed between the plateand the cone so that the gap is completely filled. The temperature isallowed to stabilize at 100° F. (37.8° C.) for about 30 seconds. Thetest is started by selecting the rpm for 10 seconds⁻¹ shear rate andrecord on the strip chart recorder. The shear stress is recorded at 10minutes after the point when the maximum shear stress is reached.Viscosity (poise)=shear stress (dynes/cm²) divided by shear rate(second⁻¹).

2. Liquid/Solid Stability Measurement

The sample of the test composition is heated until it completely melts(about 160 F. (71.1° C.) and is thoroughly mixed. The sample is thenpoured into centrifuge tubes. The samples then are allowed torecrystallize for 24 hours at 100° F. (37.8° C.) in a controlledtemperature room. The samples are then centrifuged at 60,000 rpm for onehour at 100° F. (37.8° C.). The force on the samples is 486,000 g's. Thepercent liquid separated is then measured by comparing the relativeheights of the liquid and solid phases. Liquid/solid stability(%)=100×(total volume of sample - volume of liquid that separated)/totalvolume of sample.

3. Solid Fat Content Measurement

Before determining SFC values, the sample of the polyol polyester isheated to a temperature of 158° C. (70° F.) or higher for at least 0.5hours or until the sample is completely melted. The melted sample isthen tempered at a temperature of 40° F. (4.4° C.) for at least 72hours. After tempering, the SFC value of the sample at a temperature of98.6° F. (37° C.) is determined by pulsed nuclear magnetic resonance(PNMR). The method for determining SFC values by PNMR is described inMadison and Hill, J. Amer. Oil Chem. Soc., Vol. 55 (1978), pp. 328-31(herein incorporated by reference). Measurement of SFC by PNMR is alsodescribed in A.O.C.S. Official Method Cd. 16-81, Official Methods andRecommended Practices of The American Oil Chemists Society, 3rd. Ed.,1987 (herein incorporated by reference).

4. Fatty Acid Composition

a. Polyol Polyesters

The fatty acid composition (FAC) of the polyol polyesters is determinedby gas chromatography, using a Hewlett-Packard Model S712A gaschromatograph equipped with a thermal conductivity detector and aHewlett-Packard Model 7671A automatic sampler. The chromatographicmethod used is described in Official Methods and Recommended Practicesof the American Oil Chemists Society, 3rd Ed., 1984, Procedure Ce 1-62.

b. Reduced Calorie Triglycerides

The fatty acid composition (FAC) of the reduced calorie triglycerides ismeasured by gas chromatography. First, fatty acid ethyl esters of thetriglycerides are prepared by any standard method (e.g., bytransesterification using sodium ethoxide), and then separated on acapillary column which is coated with DB-WAX stationary phase. The fattyacid ethyl esters are separated by chain length and degree ofunsaturation. A split injection is made with flame ionization detection.Quantitation is performed by use of a double internal standard method(i.e., C₉ and C₂₁ triglycerides). This method can separate fatty acidethyl esters from C₆ to C₂₄.

    ______________________________________                                        Equipment                                                                     Gas Chromatograph                                                                             Hewlett-Packard 5890, or                                                      equivalent, equipped with a                                                   split injector and flame                                                      ionization detector,                                                          Hewlett-Packard Co.,                                                          Scientific Instruments Div.,                                                  1601-T California Ave., Palo                                                  Alto, CA 94304                                                Autosampler     Hewlett-Packard 7673A, or                                     Injector        equivalent                                                    column                                                                        Column          15 m × 0.25 mm                                                          I.D., fused silica capillary                                                  column coated with DB-WAX                                                     (0.25 micron film thickness),                                                 Hewlett-Packard Co.,                                                          Scientific Instruments Div.                                   Data System     Hewlett-Packard 3350, 3000-T                                                  Hanover St., Palo Alto, CA                                                    94304                                                         Recorder        Kipp & Zonen, BD40, Kipp &                                                    Zonen                                                         Reagent                                                                       Hexane          Burdick & Jackson, or                                                         equivalent, American                                                          Scientific Products                                           ______________________________________                                    

Reference Standards

Two reference standards are used each day of operation to verify properoperation of this method. 1) A reference mixture of fatty acid methylesters (FAME) is used to check the operation of the instrument. Thisreference mixture has the following fatty acid composition: 1% C_(14:0),4% C_(16:0), 3% C_(18:0), 45% C_(18:1), 15% C_(18:2), 3% C_(18:3), 3%C_(20:0), 3% C_(22:0), 20% C_(22:1), and 3% C_(24:0). 2) A referencestandard of a commercial shortening is used to check the operation ofthe total system --ethylation and gas chromatographic analysis. Theshortening reference standard has the following fatty acid composition:0.5% C_(14:0), 21.4% C_(16:0), 9.2% C_(18:0), 40.3% C_(18:1), 23.0%C_(18:2), 2.2% C_(18:3), 0.4% C_(10:0), 1.3% C_(20:2), and 0.3%C_(22:0).

The reference mixture of FAME should be diluted with hexane and theninjected into the instrument. A new vial of FAME reference mixtureshould be opened every day since the highly unsaturated components,C_(18:2) and C_(18:3), oxidize easily. The shortening reference standardshould be ethylated with the samples prior to their analysis bycapillary gas chromatography. The results from the reference standardsshould be compared with the known values and a judgment made concerningthe completed analysis. If the results of the reference standards areequal to or within ± standard deviations of the known values, then theequipment, reagents and operations are performing satisfactorily.

Operation A. Instrumental Set-up

1. Install the column in the gas chromatograph, and set up theinstrumental conditions as in Table 1.

2. Set up the data system with the appropriate method to acquire andanalyze the data. The retention times may have to be adjusted in themethod due to instrument variations. Consult the data system referencemanual on how to do this--HP3350 User's Reference Manual. Unity responsefactors are used for each component.

3. Obtain the shortening reference standard for analysis with thesamples and ethylate it with the samples.

                  TABLE 1                                                         ______________________________________                                        INSTRUMENTAL CONDITIONS                                                       ______________________________________                                        Instrument        Hewlett-Packard 5890                                        Column            15 m × 0.25 mm I.D., coated                                             with DB-WAX, 0.25 u film                                                      thickness                                                   Column head pressure                                                                            12.5 psi                                                    Carrier gas       Helium                                                      Injector "A" temperature                                                                        210° C.                                              Split vent flow   100 ml/min                                                  Septum purge      1.5 ml/min                                                  Oven temperature profile:                                                     Initial temperature                                                                             110° C.                                              Initial time      1 min                                                       Rate 1            15° C./min                                           Final temp 1      170° C.                                              Final time 1      0 min                                                       Rate 2            6° C./min                                            Final temp 2      200° C.                                              Final time 2      0 min                                                       Rate 3            10° C./min                                           Final temp 3      220° C.                                              Final time 3      8 min                                                       Detector          FID                                                         Detector temp     230° C.                                              Make-up gas       30 ml/min                                                   Detector H.sub.2 flow                                                                           30 ml/min                                                   Detector air flow 300 ml/min                                                  ______________________________________                                    

B. Analysis of Samples - (The samples are analyzed with a doubleinternal standard.)

1. Dilute the reference mixture of FAME with hexane. The methyl estersshould be approximately 2% in hexane. Inject one microliter of thissolution via the autosampler. The results must meet the criteria in theReference Standards section.

2. Prepare the triglyceride samples to be analyzed by adding twodifferent internal standards, C₉ and C₂₁ triglycerides. (C₉ and C₂₁triglycerides are commercial standards consisting of 100% 9-carbon and21-carbon triglycerides, respectively.) The internal standards are addedto the samples at about 10% by weight of the sample. The samples(including the internal standards) are then converted to ethyl esters byany standard method.

3. Set up a sequence in the LAS data system to inject the samples.

4. Activate the autosampler to inject 1.0 microl. of the samples in thesequence. The gas chromatograph will automatically begin its temperatureprogram and the data system will collect and analyze the data for thesequence.

5. The data is analyzed with the two internal standard procedure. Theabsolute amount (mg of esters per gram of sample) of the C₆ through C₁₆components is calculated from the C₉ internal standard. The absoluteamount of the C₁₈, C₂₀, C₂₂ and C₂₄ components is calculated from theC₂₁ internal standard. Weight percentages of fatty acids are calculatedfrom these amounts.

c. 5. Ester Distribution of Polyol Polyesters

The relative distribution of the individual octa-, hepta-, hexa- andpenta- esters, as well as collectively the tetra- through mono- esters,of the polyol polyesters can be determined using normal-phase highperformance liquid chromatography (HPLC). A silica gel-packed column isused in this method to separate the polyester sample into the respectiveester groupings noted above. Hexane and methyl-t-butyl ether are used asthe mobile phase solvents. The ester groupings are quantitated using amass detector (i.e., an evaporative light scattering detector). Thedetector response is measured and then normalized to 100%. Theindividual ester groups are expressed as a relative percentage.

6. Carbon Number Profile of Reduced Calorie Triglycerides

The carbon number profile (CNP) of the reduced calorie triglycerides isdetermined by programmed temperature gas chromatography (GC) using ashort fused silica column coated with methyl silicone for analysis andcharacterization of the composition by molecular weight. The glyceridesare separated according to their respective carbon numbers, wherein thecarbon number defines the total number of carbon atoms on the combinedfatty acid residues. The carbon atoms on the glycerol molecule are notcounted. Glycerides with the same carbon number will elute as the samepeak. For example, a triglyceride composed of three C₁₆ (palmitic) fattyacid residues will co-elute with triglycerides made up on one C₁₄(myristic), one C₁₆ and one C₁₈ (stearic) fatty acid residue or with atriglyceride composed of two C₁₄ fatty acid residues and one C₂₀(arachidonic) fatty acid residue.

Preparation of the sample for analysis is as follows: 1.0 ml. of atricaprin internal standard solution (2 microg./ml.) is pipetted into avial. The methylene chloride solvent in the standard solution isevaporated using a steam bath under a nitrogen stream. Two drops of thesample (20 to 40 microg.) are pipetted into a vial. If the sample issolid, it is melted on a steam bath and stirred well to insure arepresentative sample. 1.0 ml. of bis (trimethylsilytrifluoroacetamide)(BSTFA) is pipetted into the vial which is then capped. The contents ofthe vial are shaken vigorously and then placed in a beating block(temperature of 100° C.) for about 5 minutes.

For determining the CNP/GC of the prepared samples, a Hewlett-Packard5880A series gas chromatograph equipped with temperature programming anda hydrogen flame ionization detector is used together with aHewlett-Packard 3351B data system. A 2 m. long, 0.11 mm. diameter fusedsilica capillary column coated with a thin layer of methyl silicone(Chrompak CP-SIL 5) is also used. The column is heated in an oven wheretemperature can be controlled and increased according to a specifiedpattern by the temperature programmer. The hydrogen flame ionizationdetector is attached to the outlet port of the column. The signalgenerated by the detector is amplified by an electrometer into a workinginput signal for the data system and recorder. The recorder prints outthe gas chromatograph curve and the data system electronicallyintegrates the area under the curve. The following instrument conditionsare used with the gas chromatograph:

Septum purge 1 ml./min.

Inlet pressure 5 lbs./in.²

Vent flow 75 ml./min.

Makeup carrier 30 ml./min.

Hydrogen 30 ml./min.

Air 400 ml./min.

1.0 microl. of the prepared sample is taken by a gas-tight syringe andinjected into the sample port of the gas chromatograph. The componentsin the sample port are warmed up to a temperature of 365° C. and sweptby a helium carrier gas to push the components into the column. Thecolumn temperature is initially set at 175° C. and held at thistemperature for 0.5 min. The column is then heated up to a finaltemperature of 355° C. at a rate of 25° C./min. The column is maintainedat the final temperature of 355° C. for an additional 2 min.

The chromatographic peaks generated are then identified and the peakareas measured. Peak identification is accomplished by comparison toknown pure glycerides previously programmed into the data system. Thepeak area as determined by the data system is used to calculate thepercentage of glycerides having a particular Carbon Number (C_(N))according to the following equation:

    % C.sub.N =(Area of C.sub.N /S)×100

wherein S=sum of Area of C_(N) for all peaks generated.

The Area of C_(N) is based upon the actual response generated by thechromatograph multiplied by a response factor for glycerides of theparticular Carbon Number. These response factors are determined bycomparing the actual responses of a mixture of pure glycerides ofvarious Carbon Numbers to the known amounts of each glyceride in themixture. A glyceride generating an actual response greater than itsactual amount has a response factor less than 1.0; likewise, a glyceridegenerating a response less than that of its actual amount has a responsefactor of greater than 1.0. The mixture of glycerides used (in amethylene chloride solution) is as follows:

    ______________________________________                                        Component      Carbon No.                                                                              Amount (mg./ml.)                                     ______________________________________                                        Palmitic acid  16        0.5                                                  Monopalmitin   16        0.5                                                  Monostearin    18        0.5                                                  Dipalmitin     32        0.5                                                  Palmitostearin 34        0.5                                                  Distearin      36        0.5                                                  Tripalmitin    48        1.5                                                  Dipalmitostearin                                                                             50        1.5                                                  Distearopalmitin                                                                             52        1.5                                                  Tristearin     54        1.5                                                  ______________________________________                                    

Specific Illustrations of Reduced Calorie Fat Compositions Used in thePresent Invention

The following illustrates reduced calorie fat compositions and their usein various applications in accordance with the present invention:

A. Preparation of Polyol Polyesters and Reduced Calorie Triglycerides

1. Preparation of Liquid Sucrose Polyesters from Soybean Oil

Liquid sucrose polyesters are generally prepared from soybean oil(hydrogenated to Iodine Value 107) which is converted to the respectivemethyl esters and then reacted with sucrose in the presence of apotassium carbonate catalyst and the potassium soap of the soybean oilfatty acids. The resulting soybean oil polyesters have the fatty acidcomposition (FAC), ester distribution (Esters) and viscosity (at 100°F., 37.8° C.) shown in the following table:

    ______________________________________                                        FAC              %                                                            C16:0            10.4                                                         C18:0            8.3                                                          C18:1            45.8                                                         C18:2            32.8                                                         C18:3            2.1                                                          C20:0            0.2                                                          Other            0.4                                                          Esters           %                                                            Octa             90.5                                                         Hepta            7.7                                                          Other            1.8                                                          Viscosity        Poise                                                        100° F. (37.8° C.)                                                               1.7                                                          ______________________________________                                    

2. Preparation of Liquid Sucrose Polyesters from Canola Oil

Liquid sucrose polyesters are prepared from canola oil (hydrogenated toIodine Value 90) which is converted to the respective methyl esters andthen reacted with sucrose in the presence of a potassium carbonatecatalyst and the potassium soap of the canola oil fatty acids. Theresulting canola oil polyesters have the fatty acid composition (FAC)and viscosity (at 100° F., 37.8° C.) shown in the following table:

    ______________________________________                                        FAC              %                                                            C16:0            7.0                                                          C16:1            0.3                                                          C18:0            4.6                                                          C18:1            63.0                                                         C18:2            21.8                                                         C18.3            1.3                                                          C20:0            0.4                                                          C20:1            1.0                                                          C22:0            0.2                                                          C22:1            0.1                                                          Other            0.4                                                          Viscosity        Poise                                                        100° F. (37.8° C.)                                                               1.4                                                          ______________________________________                                    

3. Preparation of Viscous Sucrose Polyesters from SoybeanHardstock/Soybean Oil

Viscous sucrose polyesters are generally prepared from a 55:45 blend ofsoybean hardstock (hydrogenated to iodine value 8) and soybean oil(hydrogenated to iodine value 107) which is converted to the respectivemethyl esters and then reacted with sucrose in the presence of apotassium carbonate catalyst and the potassium soap of the soybeanhardstock/soybean oil fatty acids. The resulting soybean hardstock/oilpolyesters have the fatty acid composition (FAC), ester distribution(Esters) and viscosity (at 100° F., 37.8° C.) shown in the followingtable:

    ______________________________________                                        FAC              %                                                            C16:0             9.6                                                         C18:0            52.7                                                         C18:1            21.3                                                         C18:2            14.7                                                         C18:3             1.0                                                         C20:0             0.5                                                         C22:0             0.2                                                         Esters           %                                                            Octa             82.1                                                         Hepta            17.9                                                         Viscosity        Poise                                                        100° F. (37.8° C.)                                                               42.9                                                         ______________________________________                                    

4. Preparation of Solid Sucrose Polyesters from Myristic Acid

Solid sucrose polyesters are generally prepared from myristic acid (atleast 99% pure) which is converted to the respective methyl esters andthen reacted with sucrose in the presence of a potassium carbonatecatalyst and the potassium soap of myristic acid. The resulting myristicacid polyesters have the fatty acid composition (FAC) and esterdistribution (Esters) shown in the following table:

    ______________________________________                                                    %                                                                 ______________________________________                                                FAC                                                                           C12:0 0.2                                                                     C14:0 99.3                                                                    C16:0 0.1                                                                     C18:0 0.2                                                                     C18:1 0.2                                                                     Esters                                                                        Octa  85.9                                                                    Hepta 12.8                                                                    Hexa  1.3                                                             ______________________________________                                    

5. Preparation of Liquid Sucrose Polyesters from Palm Kernel Oil

Liquid sucrose polyesters are generally prepared from palm kernel oil(hydrogenated to an iodine value of about 4) which is converted to therespective methyl esters and then reacted with sucrose in the presenceof a potassium carbonate catalyst and the potassium soap of the palmkernel oil fatty acids. The resulting palm kernel oil polyesters havethe fatty acid composition (FAC) and ester distribution (Esters) shownin the following table:

    ______________________________________                                                    %                                                                 ______________________________________                                                FAC                                                                           C10:0 1.0                                                                     C12:0 70.4                                                                    C14:0 18.4                                                                    C16:0 5.1                                                                     C18:0 1.0                                                                     C18:1 3.4                                                                     C18:2 0.6                                                                     Esters                                                                        Octa  84.6                                                                    Hepta 14.4                                                                    Hexa  1.0                                                             ______________________________________                                    

6. Preparation of Behenic MCT's

The behenic MCT's (A or B) are generally prepared by randomrearrangement (randomization) of tribehenin and medium chaintriglycerides using sodium methoxide as the catalyst. The crude mixtureresulting from randomization is then subjected to batch distillation (toremove a portion of the medium chain triglycerides), moleculardistillation (to remove additional medium chain triglycerides and toseparate the mono-long chain triglycerides from the di- and tri-longtriglycerides) and nonsolvent fractional crystallization (to removeadditional di-long chain triglycerides). The purified behenic MCT'sobtained have the fatty acid composition (FAC) and carbon number profile(CNP) shown in the following table:

    ______________________________________                                                      A    B                                                                        %    %                                                          ______________________________________                                        FAC                                                                           C6:0            0.8    0.3                                                    C8:0            27.3   22.9                                                   C10:0           17.8   23.4                                                   C12:0           0.3    0.4                                                    C16:0           0.4    0.2                                                    C18:0           1.8    0.6                                                    C18:1           0.1    0.1                                                    C18:1           --     0.1                                                    C20:0           4.8    2.1                                                    C22:0           46.0   45.5                                                   C22:1           0.2    0.2                                                    C24:0           1.3    1.2                                                    CNP                                                                           26              0.1                                                           28              0.6                                                           30              0.7                                                           32              1.3                                                           34              2.3    0.2                                                    36              7.4    1.4                                                    38              39.2   27.9                                                   40              36.3   48.0                                                   42              9.0    17.6                                                   44              0.6    0.9                                                    46              0.2    0.3                                                    48              0.2    0.4                                                    50              0.3    0.3                                                    52              0.7    0.2                                                    54              0.2     0.04                                                  ______________________________________                                    

7. Preparation of Stearic/Behenic MCT's

The stearic/behenic MCT's are generally prepared by randomizingcompletely hydrogenated high erucic acid rapeseed oil with medium chaintriglycerides using sodium methoxide as the catalyst, followed by batchdistillation, molecular distillation and fractional crystallization ofthe crude mixture resulting from randomization. The purifiedstearic/behenic MCT's obtained have the fatty acid composition (FAC) andcarbon number profile (CNP) shown in the following table:

    ______________________________________                                                    %                                                                 ______________________________________                                                FAC                                                                           C6:0  0.8                                                                     C8:0  31.0                                                                    C10:0 14.9                                                                    C16:0 1.9                                                                     C18:0 26.2                                                                    C18:1 0.3                                                                     C18:2 0.4                                                                     C20:0 5.8                                                                     C22:0 26.0                                                                    C24:0 0.5                                                                     CNP                                                                           26    0                                                                       28    0.5                                                                     30    0.7                                                                     32    3.2                                                                     34    24.0                                                                    36    26.4                                                                    38    27.8                                                                    40    12.2                                                                    42    2.0                                                                     44    1.0                                                                     46    0.5                                                                     48    0.6                                                                     50    0.2                                                             ______________________________________                                    

B. Clear Cooking and Salad Oils

Clear cooking and salad oils are formulated from the above soybean oilpolyesters, canola oil polyesters, behenic MCT's stearic/behenic MCT'sand soybean oil as follows:

    ______________________________________                                        Component             %                                                       ______________________________________                                        CLEAR COOKING AND SALAD OIL I*                                                Soybean or canola oil polyesters                                                                     7                                                      Behenic MCT's         12                                                      Soybean oil           81                                                      CLEAR COOKING AND SALAD OIL II**                                              Soybean or canola oil polyesters                                                                    12                                                      Stearic/behenic MCT'S 20                                                      Soybean oil           68                                                      ______________________________________                                         *at 70° F. (21.1° C.)                                           **at 50° F. (10° C.)                                       

C. Frying Oils and Potato Chips

Frying oils for potato chips are formulated from the above soybean oilpolyesters, soybean hardstock/oil polyesters, behenic MCTs andstearic/behenic MCTs as follows:

    ______________________________________                                        Component           %                                                         ______________________________________                                        FRYING OIL I                                                                  Soybean hardstock/oil                                                                             22                                                        polyesters                                                                    Soybean oil polyesters                                                                            28                                                        Stearic/behenic MCTs                                                                              43                                                        Behenic MCTs (A)     7                                                        FRYING OIL II                                                                 Soybean oil polyesters                                                                            50                                                        Behenic MCTs (A)    50                                                        ______________________________________                                    

Ninety grams of sliced potatoes are fried in 11 kg. of frying oil I orfrying oil II at a temperature of 365° F. (185° C.) for 3 minutes, 5seconds, to provide potato chips.

D. Chocolate-Flavored Candy Bar

a blend containing the myristic acid polyesters is prepared from thefollowing ingredients:

    ______________________________________                                        Ingredient            Grams                                                   ______________________________________                                        Chocolate liquor      3.6                                                     Cocoa powder (11% cocoa butter)                                                                     5.1                                                     Sweet cream powder (72% milkfat)                                                                    2.4                                                     Lecithin              0.1                                                     Natural/artificial butter flavors                                                                    0.14                                                   Sucrose powder (extra fine)                                                                         15.7                                                    Myristic acid polyester                                                                             14.0                                                    ______________________________________                                    

The above blend is heated to 135° F. (57.2° C.) in a glass beaker andthen gradually cooled to 90 F. (32.2° C.) with mixing until the blendbecomes smooth and lump-free.

A blend containing the behenic MCT's is prepared from the followingingredients:

    ______________________________________                                        Ingredient            Grams                                                   ______________________________________                                        Behenic MCT's (B)     14.0                                                    Soybean lecithin       0.12                                                   Cocoa powder (11% cocoa butter)                                                                     7.7                                                     Nonfat milk solids    9.0                                                     Vanilla flavor         0.18                                                   Sucrose               28.0                                                    ______________________________________                                    

The above blend is passed twice through a 4-roll mill to reduce theparticle size of the sucrose. The roll milled behenic MCT-containingblend is then combined with the myristic acid polyester-containingblend, poured at 90° F. (32.2° C.) into chocolate bar molds, cooled at50° F. (10° C.) for 48 hours and then gradually warmed to 70° F. (21.1°C.) in a styrofoam cooler. The tempered chocolate-flavored candy barsare then demolded.

E. Margarine-Like Spread

The aqueous phase of the margarine-like spread is formulated from thefollowing ingredients:

    ______________________________________                                        Ingredient            Grams                                                   ______________________________________                                        Water                 150                                                     Distilled mono- and diglycerides                                                                    1.5                                                     Lecithin              1.0                                                     Natural/artificial butter flavors                                                                   0.09                                                    Salt                  11.0                                                    Potassium Sorbate     0.12                                                    Citric acid           0.04                                                    ______________________________________                                    

The above aqueous phase ingredients are dissolved in the water and thenheated to 130° F. (54.4° C.).

The fat phase of the margarine-like spread is formulated from thefollowing ingredients:

    ______________________________________                                        Ingredient            Grams                                                   ______________________________________                                        Stearic/behenic MCT's 332.5                                                   Palm kernel oil polyesters                                                                          166.2                                                   Soybean hardstock/oil polyesters                                                                    166.0                                                   Soybean oil polyesters                                                                              166.0                                                   ______________________________________                                    

The aqueous phase ingredients are blended into the fat phase ingredientsat 130° F. (54.4° C.) under high shear mixing conditions using an Agimixer equipped with a homogenizer head, a rotating bowl and Teflonscrapper blades to remove emulsified and crystallized material from theinside wall of the bowl. Chilled water is sprayed on the outside wall ofthe bowl to cool it. As the mass in the bowl is cooled to approximately67° F. (19.4° C.), the viscosity increases to that of a typical softmargarine consistency. The emulsified/crystallized material is filledinto plastic tubs, placed in a 32° F. (0° C.) bath for 1 hour and thenstored for 48 hours in a 40° F. (4.4° C.) constant temperature room toprovide a soft, spreadable margarine-like product.

F. Frozen Strawberry-Flavored Dessert

A frozen strawberry-flavored dessert is formulated from the followingingredients:

    ______________________________________                                        Ingredient           Grams                                                    ______________________________________                                        Frozen strawberries  700                                                      (thawed and homogenized)                                                      Palm kernel oil polyesters                                                                         128                                                      Stearic/behenic MCT's                                                                              192                                                      Polyglycerol ester emulsifier                                                                       18                                                      Propylene glycol monostearate                                                                       8                                                       Dariloid (gum mixture)                                                                              4                                                       Sucrose              320                                                      Vanilla extract       4                                                       Dried cream extract   10                                                      Skim milk            569                                                      Artificial cream flavors                                                                            2                                                       ______________________________________                                    

Except for the strawberries, the above ingredients are homogenized at120°-135° F. (48.9°-57.2° C.) for about 10 minutes under high shearmixing using the same equipment as in the margarine-like spread example,but with chilled propylene glycol as the coolant. This homogenizedmixture is cooled to 63° F. (17.2° C.) and then a portion (approximately500 g.) of the strawberries are added. This homogenized mixture iscooled further to 40° F. (4.4° C.) and then the remaining portion of thestrawberries are added. After further cooling, this mixture starts tofreeze at 30° F. (-1.1° C.). After freezing begins, this mixture iscooled for about 10 additional minutes before being transferred intoone-pint containers. This entire cooling/freezing process takes place inabout 30 minutes. The pint containers are stored for 2 to 3 hours atapproximately -40° F. (-40° C.) to provide the final ice cream-likefrozen strawberry-flavored dessert.

What is claimed is:
 1. A firm chocolate-flavored product having fat andnonfat ingredients wherein from about 10 to about 100% of the total fatcomprises a reduced calorie fat composition comprising from about 45 toabout 55% of a sucrose octaester having at least about 90% myristic acidgroups and from about 45 to about 55% reduced calorie triglycerideshaving at least about 80% C₃₈ to C₄₂ triglycerides, from about 40 toabout 50% C₈ to C₁₀ saturated fatty acids and from about 40 to about 60%behenic acid, wherein said reduced calorie triglycerides are selectedfrom the group consisting of MMM, MLM, MML, LLM, LML and LLLtriglycerides, and mixtures thereof; wherein M is a saturated fatty acidresidue selected from the group consisting of C₆ to C₁₀ saturated fattyacids, and mixtures thereof; wherein L is a saturated fatty acid residueselected from the group consisting of C₂₀ -C₂₄ saturated fatty acids andmixtures of C₁₈ to C₂₄ saturated fatty acids; and wherein said reducedcalorie triglycerides comprise: (1) at least about 85% combined MLM,MML, LLM and LML triglycerides; and (2) up to about 15% combined MMM andLLL triglycerides.